Anderson: The Bruins and the dynasty that should have been

Six years ago to the day, the Bruins and their fans, after 39 years of suffering and with a litany of embarrassments in between championships, were on top of the hockey world.

In a run that featured three Game 7s and surely took half a decade off everybody’s lives, that moment of euphoria following the 4-0 Game 7 final over the Canucks remains hard to put into words. The wire-to-wire season that Tim Thomas, named the Conn Smythe winner for his two-month warpath and the Vezina as the league’s top regular-season goalie, had, remains hard to put into words. But, the appreciation for that moment was there in street celebrations and the most attended parade in Boston sports history. It was there a year later, too, even as the Bruins were bounced from a potential repeat in a round-one showdown with the Capitals. Two years later, you noted the date, but you were far too concerned with the run the club was on, which ended in a six-game Cup Final loss to the Blackhawks.

But as the ‘happy’ in that happy anniversary hits the six-year mark, that celebration feels a bit more like 60 years ago these days, and it’s become increasingly difficult to look back on what was for the Black and Gold without a heavy sigh and thoughts of what could have, or maybe should have, been in Boston.

Let’s just say it: Those Bruins should have captured more than one Stanley Cup.

It’s the hardest trophy in sports to win. You don’t need to tell me that. We all know it.

But that excuse has not stopped the Penguins, Kings, or Blackhawks from multiple championships over this same timespan. Since 2009, the Penguins have captured three Stanley Cups (2009, 2016, 2017), same for the Blackhawks (2010, 2013, and 2015), and the Kings have nabbed two (2012 and 2014). The outlier in this nine-year sample remains the 2011 Bruins.

But the Bruins were not a one-year pony. They should have been anything but.

The core of the Bruins -- featuring Patrice Bergeron, David Krejci, Milan Lucic, Nathan Horton, and the budding superstar Brad Marchand up front, and captain Zdeno Chara, Johnny Boychuk, and even Dennis Seidenberg (a minute-eating beast if there ever was one) on the backend -- were all either entering or already in the absolute prime of their NHL careers. The club had an answer behind the aging Thomas in Tuukka Rask. Franchise forward Tyler Seguin, the second overall pick from 2010, was only getting better (he was a 20-year-old spare part when the Bruins won it all), and future top-pairing defenseman Dougie Hamilton was drafted nine days after the Bruins won that aforementioned Game 7 in Vancouver.

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Tankers for just two seasons (2005-06 and 2006-07), a series of favorable contracts and draft gifts from the Maple Leafs gave the Bruins what looked like a decade-long championship window in place. Led by their current cast of characters -- and with a star center, franchise defenseman, and elite goalie in waiting -- 2011 was not going to be the last Cup lifted by the Bruins. Not a chance.

(When people today talk about the Celtics being set for the future thanks to their treasure chest of lottery picks -- and with more coming -- it’s only because they can’t remember how easy the Bruins had it made.)

But it didn’t happen.

In fact, 2013’s Game 6 collapse on home ice -- with the Blackhawks scoring two goals in 17 seconds to steal the game and Cup -- was the last time we saw the team even reach the fourth round.

So what the hell went wrong?

Have a minute and a pack of cigarettes? ‘Cause explaining this mismanagement ain’t easy.

First, the biggest reason for this comes back to the mishandling of those future franchise pieces.

Although it really began with Phil Kessel, a player that’s been part of two championship teams in the last two years now, the departures of the key returns in the Kessel deal with the Leafs -- Seguin, Hamilton, and Jared Knight, drafted 32nd overall in 2010 -- came with absolute disastrous returns for the Bruins.

At least when it came to maintaining that Cup-contending balance that the Bruins sought as returns.

Hindsight is, of course, all too easy when it came to the Seguin trade. And while I think it’s fair to judge the quickness with which the Bruins dumped Seguin at the first sign of danger (versus the way the Chicago Blackhawks stuck it out with Patrick Kane’s off-ice issues years ago now), the real criticism should come with the fact that the Bruins just did not get enough of a return in that trade.

Loui Eriksson was a fair headlining piece, but the other players the Bruins plucked from the Stars -- Matt Fraser, Joe Morrow, and Reilly Smith -- did or have done almost nothing in Boston.

In fact, as far as directly involved players go, only Morrow, primarily a seventh defenseman for the Bruins during his time with the NHL club (65 games in the last three NHL seasons), remains with the club. He’s a restricted free agent for an already crowded Boston blue line. Jimmy Hayes, acquired in exchange for Smith back in July 2015, is also with the club, but could be buried in the minors or moved in a trade, as his Boston stint has been nothing short of a nightmare for the Dorchester native.

So while Seguin seems primed for 90-point years for the next decade, the B’s final return could quite possibly read Hayes (acquired for Smith) and Morrow by the time the puck drops on the 2017 season. Or, better yet, both players could be elsewhere, depending on how the expansion process falls out.

It remains an utter failure of a trade for this organization.

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(If you’re looking for some sort of comfort, the Hamilton trade, which amounted to Zach Senyshyn, Jakob Forsbacka Karlsson, and Jeremy Lauzon, looks better in the now. But that’s largely a finish yet to be written, really, as the three pieces haven’t made NHL impacts just yet.)

But in regards to the young talents shipped out of town, there’s something to be said about players such as Blake Wheeler (2011) and Smith (2015), who struggled to find their footing here, but evolved into leaders and certain top-six talents in other cities. Was it a mere matter of utilization by their new coach versus the now-fired Claude Julien? Was it a system issue? Or is it that the expectations in Boston are impossibly high, by the coach, the front office, and the fans, that a move to a different city -- Atlanta-then-Winnipeg in the case of Wheeler and Florida in the case of Smith -- allow a more complete and mistake-tolerant development path? The Wheeler trade made the Bruins better in the sense that they acquired a veteran piece that allowed them to become a more complete team throughout their playoff runs in Rich Peverley, but the Smith for Hayes trade really said more about an organization’s unwillingness to wait it out with a young player on the verge of a substantial raise (Smith’s cap-hit was set to go up to $3.425 million in 2015). That latter point also seemed to play a factor in the Seguin deal, too, as he was set to make over $5 million beginning in the fall before his deal.

Losing a high-skilled young player is doubly painful when you don’t have much behind him in the pipeline, which is exactly where the Bruins found themselves for years when it came to their drafting.

The pick that’s still just completely hammered by people (even to this day!) is the selection of Zach Hamill with the eighth overall pick in 2007. Logan Couture went just one pick after that. Ryan McDonagh went four after Hamill, and Kevin Shattenkirk went six picks later. The list goes on and on, too. Of their entire 2007 draft class, which included six players in total, only Hamill and Tommy Cross have suited up for an NHL game. Hamill skated in 20 (but is long gone), while Cross has played in three. 23 games. Twenty-three. The 2008 class has over 300 games games of NHL experience in total between four players -- Joe Colborne, Michael Hutchinson, Max Sauve, and Jamie Arniel -- but just two of those games came with the Bruins. Both were one-game cups of NHL coffee for Arniel and Sauve. Boston’s crown jewel of their five-player 2009 class was Jordan Caron. He had 28 points in 134 games for the Bruins. Kyle Palmieri, taken one pick after Caron, had 26 goals in 80 games for the Devils last year.

That three-year drafting blackhole was something else, and it wasn't even the end of it.

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2012 was when they took a gamble on Malcolm Subban in the first round. It almost seemed like a borderline spiteful pick at the time, too, as Subban's selection came just weeks after the word that Thomas was going to walk away from the Bruins and take the 2012-13 season off to focus on his life outside of hockey. Two-time Stanley Cup winner Matt Murray went 59 picks after Subban and Frederik Andersen went 63 picks later. Subban has started two NHL games during his time with the Bruins. He has not finished either one of them.

The club's drafting began to improve in 2014 (although the 2013 class seems to have a few possible gets for the Black and Gold), and has continued to be a point of emphasis since Don Sweeney, who has a background in player and development, took over for Peter Chiarelli as the B's general manager in 2015, but that straight-up ghost town of a prospect pool accelerated their downfall.

Specifically when it came to the cap-hell that the club routinely worked themselves into.

When you don’t have prospects knocking at the door, you re-sign your pending free agents. When said pending free agents are part of a championship winner and then potential repeat contender, they get healthy raises. In some cases, they get raises that are not fitting of what they really are and will be down the road. This was life for the Bruins -- whose love for their players from a championship team, supporting cast or star player, will probably go down as one of the most damaging in recent history -- for far too long.

It even extended to the new-to-them players that the club had long lusted after.

When the dust cleared on the Seguin trade in 2013, Jarome Iginla, who nixed a trade to the Black and Gold just months earlier, came to the Bruins in search of his first Stanley Cup. It was the perfect one-year deal for Iginla and the B’s. Iginla would count against the Boston cap for just $1.8 million, but his contract could have been worth up to $6 million in bonuses. Most of those bonuses would be met with simple games played milestones, too, so the cap-crunch was inevitable. Think about it: Iginla made $3.75 million in bonus money alone by the time he appeared in just 10 games for the Bruins. By the end of the year, one year of Iginla cost you just $250,000 less than it would have to have kept Seguin at his $5.75 million, but with the penalties that didn’t come until the following season (also known as when Iginla decided to ditch you for a three-year pact with the Avalanche).

It was Iginla’s bonus money, along with some other minor bonus overages that came against Boston’s cap the following season, that proved to be the impetus for the trade that saw the Bruins move their No. 2 defenseman, Johnny Boychuk, to the New York Islanders for picks just to begin the year under the cap.

That trade was also a product of overpayments to bottom-six talents -- in no world should your fourth-line center (Gregory Campbell) count against your cap for $1.6 million, nor should you commit four years to over-30 guys with physically taxing roles like the Bruins did with Chris Kelly and Seidenberg -- and the Bruins paid for it by hamstringing their cap flexibility and thus putting an end to their Stanley Cup window with a thinned out, incomplete roster.

This was written off as the cost of doing business to contend (they told us that the salary cap makes it impossible to keep a Stanley Cup squad together), and even as the capable bodies left, the B’s denial in regards to their situation as an aging, sinking ship didn’t help. It plunged them further into an abyss.

The Bruins loved, er -- were forced -- to go hunting for scraps in the bargain bins of free agency. Simon Gagne, after a year away from hockey, beat out actual ghoul Ville Leino for a spot on the 2014-15 roster. It was the club’s low-risk, high-reward Hail Mary attempt on an Iginla replacement. Matt Irwin was the Hamilton gamble, signed to a one-year contract as a potential fix on the Boston blue line. It’s worth noting, of course, that neither Gagne (retired) nor Irwin (banished to the minors after a couple of games) finished their respective seasons in a Boston sweater. Irwin bounced back with a Stanley Cup run with Nashville this past season.

And when that didn’t work, the Bruins often mortgaged more future draft picks on gambles like Brett Connolly (nine goals in 76 games for Boston before he was released by the team), Andrej Meszaros (a healthy scratch for most of the 2014 playoffs), and Joe Corvo (a disaster). The Bruins traded four draft picks -- even though they were never higher than a second-round pick -- for those three players alone. But this wasn’t a strictly Chiarelli trait, as Sweeney traded a combined four draft picks to acquire over-30 free-agents-to-be John-Michael Liles and Lee Stempniak at the 2016 trade deadline. Like the cheap, plug-in trades that came before, neither one of those deals worked for the Bruins.

At a certain point, the Bruins became a team that was constantly playing catch-up… with themselves.

Instead of competing with a Pittsburgh or a Chicago for multiple championships, the Bruins were instead losing negotiations, trades, and direction. They often chose the wrong players -- both to target in trades (as mentioned above), and when it came to who was re-signed versus who was moved and when they were moved. (If the club could have one do-over, I truly believe it would have been extending Boychuk over Seidenberg.) In their battle against time to maximize their championship window with Chara as a truly elite defenseman, the Bruins misjudged where they and the player were. They’ve since wasted those years, along with some prime years of Bergeron, Krejci, Marchand, and Rask. They kept Claude Julien twisting in the wind when a clean break probably would have made sense for both the organization's direction and certain players. They’ve also entered purgatory as a team that’s still too good to tank, but not good enough to win a Stanley Cup.

It was a four-year run of mismanagement and miscalculations worthy of a case study on how not to run a franchise.

So, happy anniversary, sure.

But this should not have been the only championship date to this core’s name.